A sustainable and simple catalytic system for direct alkynylation of C(sp(2))-H bonds with low nickel loadings

Chemical Communications : Chem Comm
Yue-Jin LiuBing-Feng Shi

Abstract

A sustainable and simple catalytic system for the atom-economical alkynylation of benzamides with low nickel loadings is described. No organic or metallic oxidants and expensive ligands are required. A broad range of benzamides and bromoalkynes bearing various synthetically useful functional groups are compatible with this reaction. The versatility of this operationally simple protocol has been further demonstrated by the controllable mono- and di-alkynylation. Importantly, substrate/catalyst ratios of up to 200, and a turnover number of 196 were achieved, highlighting the potential of this protocol for synthetic applications.

References

Oct 3, 2002·Journal of the American Chemical Society·Brian D DangelDalibor Sames
May 15, 2003·Chemical Reviews·Ei-ichi Negishi, Luigi Anastasia
Sep 22, 2005·Journal of the American Chemical Society·Vladimir G ZaitsevOlafs Daugulis
Jun 2, 2007·Journal of the American Chemical Society·Ilya V SereginVladimir Gevorgyan
May 15, 2009·Chemical Reviews·Denise A ColbyJonathan A Ellman
Jun 26, 2009·Accounts of Chemical Research·Olafs DaugulisDmitry Shabashov
Jun 27, 2009·Organic Letters·Mamoru TobisuNaoto Chatani
Sep 11, 2009·Organic Letters·Naoto MatsuyamaMasahiro Miura
Nov 7, 2009·Angewandte Chemie·Jonathan P BrandJérôme Waser
Nov 11, 2009·Angewandte Chemie·François Besselièvre, Sandrine Piguel
Jan 19, 2010·Chemical Reviews·Thomas W Lyons, Melanie S Sanford
Jan 22, 2010·Journal of the American Chemical Society·Teresa de Haro, Cristina Nevado
Feb 24, 2010·Journal of the American Chemical Society·Dmitry Shabashov, Olafs Daugulis
Mar 2, 2010·Angewandte Chemie·Alexander S Dudnik, Vladimir Gevorgyan
Sep 22, 2010·Journal of the American Chemical Society·Keary M EngleJin-Quan Yu
Nov 6, 2010·Chemical Reviews·Chang-Liang SunZhang-Jie Shi
Mar 11, 2011·Chemical Society Reviews·Lindsay McMurrayMatthew J Gaunt
Jun 10, 2011·Chemical Society Reviews·Rafael Chinchilla, Carmen Nájera
Jul 28, 2011·Journal of the American Chemical Society·Yusuke AnoNaoto Chatani
Sep 8, 2011·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Yoshiaki Nakao
Dec 15, 2011·Accounts of Chemical Research·Keary M EngleJin-Quan Yu
Apr 20, 2012·Chemical Society Reviews·Jonathan P Brand, Jérôme Waser
Aug 14, 2012·Angewandte Chemie·Junichiro YamaguchiKenichiro Itami
Sep 1, 2012·Chemical Reviews·Percia Beatrice ArockiamPierre H Dixneuf
Sep 22, 2012·Angewandte Chemie·Nadine KuhlFrank Glorius
Jan 29, 2013·Journal of the American Chemical Society·Shu-Yu ZhangGong Chen
Feb 15, 2013·Journal of the American Chemical Society·Jian HeJin-Quan Yu
Mar 21, 2013·Angewandte Chemie·Mayuko NishinoMasahiro Miura
Apr 16, 2013·Journal of the American Chemical Society·Rui ShangEiichi Nakamura
Jun 12, 2013·Journal of the American Chemical Society·Alison M SuessShannon S Stahl
Oct 19, 2013·Chemical Communications : Chem Comm·Beatriz UronesJuan C Carretero
Jan 1, 2014·Journal of the American Chemical Society·Yoshinori Aihara, Naoto Chatani
Jan 23, 2014·Journal of the American Chemical Society·Xuesong WuHaibo Ge
Feb 13, 2014·Angewandte Chemie·Chao Feng, Teck-Peng Loh

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Citations

Feb 11, 2016·Organic Letters·Vinod G LandgeEkambaram Balaraman
Jan 30, 2016·Angewandte Chemie·Zhixiong RuanLutz Ackermann
May 20, 2015·The Journal of Organic Chemistry·Jun YiFuwei Li
May 21, 2015·Organic Letters·Wei-Hao Rao, Bing-Feng Shi
May 6, 2015·Organic Letters·Qiangqiang YanYuhong Zhang
Aug 6, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Vinod G LandgeEkambaram Balaraman
Aug 12, 2015·Organic Letters·Zhuo-Zhuo ZhangBing-Feng Shi
Aug 31, 2016·Topics in Current Chemistry·Junichiro YamaguchiKenichiro Itami
Oct 23, 2015·Organic Letters·Nicolas SauermannLutz Ackermann
Oct 5, 2016·Organic Letters·Vinod G LandgeEkambaram Balaraman
Mar 28, 2017·ChemSusChem·Rahul A JagtapBenudhar Punji
Jan 1, 2017·Chemistry : a European Journal·Lucien D CaspersBoris J Nachtsheim
Feb 9, 2017·Chemistry : a European Journal·Gianpiero CeraLutz Ackermann
Dec 27, 2016·Chemistry : a European Journal·Shrikant M KhakeBenudhar Punji
Feb 10, 2017·Angewandte Chemie·Zhixiong RuanLutz Ackermann
Apr 11, 2018·Organic & Biomolecular Chemistry·Xueli WangLixin Xia
Sep 5, 2017·Chemical Communications : Chem Comm·Sheng-Yi YanBing-Feng Shi
Mar 27, 2018·Chemistry, an Asian Journal·Lucien D Caspers, Boris J Nachtsheim
Jun 20, 2018·Chemical Communications : Chem Comm·Vinod G LandgeEkambaram Balaraman
Jul 24, 2018·Chemical Society Reviews·Carlo SambiagioMichael Schnürch
Sep 5, 2018·Organic & Biomolecular Chemistry·Debashruti BandyopadhyayS Peruncheralathan
Jan 13, 2017·Angewandte Chemie·Haiyan FuJin-Quan Yu
Jan 31, 2018·Chemical Communications : Chem Comm·Guangbin JiangHuanfeng Jiang
Apr 21, 2018·Chemical Science·Brandon E HainesDjamaladdin G Musaev
Aug 2, 2017·Chemical Communications : Chem Comm·Zhixiong RuanLutz Ackermann
Dec 6, 2017·Angewandte Chemie·Tobias GenschFrank Glorius
May 31, 2017·Organic Letters·Ruhuai MeiLutz Ackermann
Jan 4, 2017·Journal of the American Chemical Society·Hélène M-F ViartRichmond Sarpong

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